When you think spooky and scary,Disneyprobably isn’t the first word that comes to mind. That’s not to say the House of Mouse hasn’t delivered some pure nightmare fuel over the years, such as Judge Doom (Christopher Lloyd) fromWho Framed Roger Rabbit, the Monkey fromToy Story 3, andjust about everything inReturn to Oz. However, one of the company’searliest, spookiest, and all around best stories turned seventy-five this year, that of course beingThe Adventures of Ichabod and Mr. Toad. Keep in mind I’m only referring to the “Ichabod Crane” half of the film, as the “Mr. Toad” portion can go pound sand since it is responsible for one of the worst Disneyland rides ever made.
The Adventures of Ichabod and Mr. Toadmay only be a quarter away from turning a hundred, but its depiction of “The Legend of Sleepy Hollow” still holds upand is likely most’s introduction to the story, since theTim Burtonfilm andsurprisingly great cult-favorite TV seriesare both geared toward much older audiences. Even to this day, the story’s notorious villain, The Headless Horseman, still makes an appearance at the Disney parks, usually leading the seasonal Halloween parade. It’s a timeless classic that embraces an important piece of American folklore, and it reigns supreme as an excellent family-friendly Halloween story that still features some pretty good scares and tension.

What is “The Legend of Sleepy Hollow” About?
Midway throughThe Adventures of Ichabod and Mr. Toad, “The Legend of Sleepy Hollow” begins, which primarily follows a school teacher named Ichabod Crane (Bing Crosby) in the late 1700s United States. Crane quickly develops a reputation as a popular member of the local community, which puts him at odds with the New England town’s resident brute, Brom Bones (also voiced by Bing Crosby). The two’s rivalry reaches a peak when they both try to win over the heart of Katrina van Tassel, the town’s beautiful (and enormously wealthy) bachelorette.
Already the set-up here is interesting, as Ichabod Crane and Brom Bones are not your typical protagonist and antagonist. At first glance it seems that way, as Ichabod is a goofy and lovable source of levity while Brom clearly relishes in his selfish tendencies. However, the story makes no secret that Ichabod’s main purpose for wanting to marry Katrina is to inherit her fortune, while Brom doesn’t appear to be as focused on that aspect.Two fairly complex characters for a short story intended for children, yet “The Legend of Sleepy Hollow” only gets more interesting toward the surprisingly scary finale.

The Headless Horseman Chase in ‘The Adventures of Ichabod Crane’ is a Spooktacular Ending
The bulk of “The Legend of Sleepy Hollow” sees Brom trying to outwit Ichabod to no avail, and he makes one last attempt by trying to scare Ichabod out of town. In perhaps the catchiest scary song ever recorded,Brom gleefully regales the tale of The Headless Horseman - the self-explanatory monster who supposedly stalks the roads at night. The story properly shakes up Ichabod, and the horse ride home is destined to change just about everything.
The true highlight of the story is when Ichabod and his horse are prancing home through the forest, which begins with the music taking a break to introduce plenty of bizarre and unsettling sounds of the desolate woods.The sound design and foley work during this entire sequence is remarkable, and the slick animation accompanying it makes it even better. It’s so convincing that it tricks Ichabod into thinking the forest is filled with monsters, only to discover the sources of the sounds were mundane things like frogs and plants. Ichabod and his horse have a good laugh about it, until they notice a much more sinister laughter that isn’t coming from any of them.

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The terrifying cackle is coming from none other than the very real and very voracious Headless Horseman, who begins chasing Ichabod throughout the woods ina sequence that expertly balances cartoon slapstick with a tense slasher chase.The Horseman is genuinely one of the best depictions of the character in film or television just because of his simplicity. He has no motive, no origin, no backstory to speak of. He’s just a dedicated deity who takes immense pleasure in tormenting his victims witha very eerie Jack O' Lantern head.
This leads into one of the most surprising elements ofThe Adventures of Ichabod and Mr. Toad- the ending. We daren’t spoil too much for those of you yet to experience this terrific tale, but it doesn’t end in the way you might expect. An ending that’s surprisingly nuanced and ambiguous, and makes one thing perfectly clear -You can’t reason with a headless man(cue the catchy Bing Crosby song).
The Adventures of Ichabod and Mr. Toad
The Adventures of Ichabod and Mr. Toadis available to stream on Disney+.